A General Procedure for the Synthesis of 2-Substituted Pyrimidine-5-Carboxylic Esters

Abstract

A method for the synthesis of 2-substituted pyrimidine-5-carboxylic esters is described. The sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (3) has been found to react with a variety of amidinium salts to afford the corresponding 2-substituted pyrimidine-5-carboxylic esters.

One‐Pot Three‐Component Synthesis of 2‐Amino Pyrimidines in Aqueous PEG‐400 at Ambient Temperature

“…. The cyclocondensation of chalcones with amidines at refluxed conditions in presence of triethylamine in ethanol , KOH in ethanol or in methanol , in presence of peroxide , sodium isopropoxide in isopropanol , and dimethylformamide is the most widely way for the synthesis of pyrimidines. These synthetic routes have drawbacks, as they need amidines, unsaturated ketones, aryl‐β‐vinyl imines, sulfonium salts, and imidazolium derivatives, which make the routes time‐consuming.…”

Synthesis of [14C] labeled 2‐methoxypyrimidine‐5‐carboxylic acid

“…[13][14][15][16] However, a few direct approaches leading to pyrimidine ring that lacks substitution at 4-position have been reported. [17][18][19] Our approach to compound 2 is as depicted in Scheme 1. In parallel, the sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (7) was synthesized by the condensation of methyl formate with methyl 3,3-dimethoxypropionate in the presence of NaH as described in the literature.…”

“…In parallel, the sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (7) was synthesized by the condensation of methyl formate with methyl 3,3-dimethoxypropionate in the presence of NaH as described in the literature. 19 The sodium salt 7 was reacted with […”

New Strategies for the Synthesis of Pyrimidine Derivatives

“…[ 21] In this report, a number of pyrimidine derivatives were formed by direct condensation of amidinium chlorides 20 with the sodium salt of 2-dimethoxymethyl-3-hydroxy-acrylic acid methyl ester (19,Scheme 9). This 1,3-dicarbonyl equivalent was prepared by condensation of methyl formate with 3,3-dimethoxypropionate.…”